Publications

Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile

Pickhardt, W. and Wohlgemuth, M. and Grätz, S. and Borchardt, L.

JOURNAL OF ORGANIC CHEMISTRY
Volume: 86 Pages: 14011-14015
DOI: 10.1021/acs.joc.1c00253
Published: 2021

Abstract
1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT CN) was synthesized mechanochemically at room temperature. The coupling of hexaketocyclohexane and diaminomaleonitrile was conducted in 10 min by vibratory ball milling. The effects of milling parameters, acids, dehydrating agents, and liquid-assisted grinding were rationalized. With 67%, the yield of this mechanochemical approach exceeds that of state-of-the-art wet-chemical syntheses while being superior with respect to time-, resource-, and energy-efficiency as quantified via green metrics. © 2021 The Authors. Published by American Chemical Society.

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